Cheap Flight Tickets from San Jose (SJO) to Chicago (MDW), Starting at $422

Good to Know: Cheapest and Fastest SJO - MDW Flights

Useful information for finding best airline tickets from Juan Santamaria International to Chicago Midway International on your next trip.

Cheapest Round Trip Flight

$422

WN Southwest Airlines • 1 stop • 12h 30m

Oct 22 – Oct 27

The cheapest round trip flight from San Jose to Chicago (SJO-MDW-SJO) is currently $422

🔍 Search Flights

Fastest Flight

12h 30m

The fastest nonstop flight from San Jose to Chicago (SJO-MDW) takes 12h 30m

Top Airlines Flying from San Jose to Chicago

Southwest Airlines-WN

Southwest Airlines

Latest Flight Deals from San Jose (SJO) to Chicago (MDW)

Compare and book low fare round-trip air tickets from San Jose to Chicago. Ideal for travelers with confirmed return itineraries.

Oct 22 - Oct 27, Economy
WN
San Jose → Chicago
12h 30m
1:30 PM - 10:20 PM • 1 stop
WN
San Jose → Chicago
17h 10m
10:10 AM - 7:40 PM • 2 stops
$422
Southwest Airlines
Oct 22 - Oct 27, Economy
WN
San Jose → Chicago
12h 30m
1:30 PM - 10:20 PM • 1 stop
WN
San Jose → Chicago
13h 35m
12:25 PM - 7:40 PM • 1 stop
$422
Southwest Airlines
Oct 22 - Oct 27, Economy
WN
San Jose → Chicago
23h 45m
9:00 AM - 12:25 AM • 1 stop
WN
San Jose → Chicago
17h 10m
10:10 AM - 7:40 PM • 2 stops
$422
Southwest Airlines
Oct 22 - Oct 27, Economy
WN
San Jose → Chicago
17h
9:00 AM - 8:20 PM • 2 stops
WN
San Jose → Chicago
12h
5:45 AM - 12:05 PM • 1 stop
$427
Southwest Airlines
Oct 22 - Oct 27, Economy
WN
San Jose → Chicago
17h 20m
1:30 PM - 1:10 AM • 2 stops
WN
San Jose → Chicago
17h 10m
10:10 AM - 7:40 PM • 2 stops
$427
Southwest Airlines
Oct 22 - Oct 27, Economy
WN
San Jose → Chicago
16h 55m
9:00 AM - 8:15 PM • 2 stops
WN
San Jose → Chicago
17h 10m
10:10 AM - 7:40 PM • 2 stops
$427
Southwest Airlines

Fly from San Jose to Chicago with the Best Airfare Deals on FareLeaders

Looking for a cheap last-minute deal or the best round-trip flight from San Jose to Chicago? Find the biggest savings on one-way and round-trip tickets right here.

FAQs on San Jose to Chicago Flights

What are the airports in San Jose?
SJO
What’s the most popular airline flying from SJO to MDW?
The most popular airline flying from San Jose to Chicago are
Can I fly from SJO to MDW non-stop?
NO
Which airlines fly nonstop between San Jose and Chicago?
The non-stop flights between San Jose and Chicago are .
What’s the earliest departure time from SJO to MDW Airport?
The earliest flight leaves SJO at 9:00 am and lands in MDW - Chicago Midway International
What are the airports in Chicago?
ORD,MDW
Can I make changes to my San Jose to Chicago flight tickets or cancel them on FareLeaders.com?
No. We are an airfare comparison site. All the tickets are booked by the travel agent offering the flight deal and any changes or cancellations to be made are directly done directly by them or the airlines.
Can I cancel my flight tickets from SJO to MDW?
Read the fare rules of the San Jose to Chicago air tickets booked. Some airlines allow you to cancel the tickets within a stipulated time period with a cancellation fee.
Which airline alliances offer flights from San Jose and Chicago?
operate flights between San Jose and Chicago
How long does a flight from San Jose to Chicago take?
It takes approximately 5 hour to fly non-stop from SJO to MDW, which is 2199.5 miles by air.
Which airlines provide the cheapest flights from San Jose (SJO) to Chicago (MDW) ?
In the past couple of days, the cheapest tickets to MDW from SJO were found on WN : USD 427
Do I need a passport to fly between SJO and MDW?
Yes
What’s the latest departure time from SJO to MDW ?
The last flight leaves SJO at 1:30 pm

Essential Information for Booking Flights from San Jose (SJO) - AI Insights

What's the cheapest airline from sjo to mdw?
You can find the cheapest flights from Juan Santamaria International Airport (SJO) to Chicago Midway International Airport (MDW) with Southwest Airlines (WN) on FareLeaders.com. Southwest Airlines offers budget-friendly flights with luxurious amenities like fine dining and suites. Book your round-trip ticket 15 days in advance to secure the best fares.
What's the popular airline to fly from sjo to mdw?
You can fly from Juan Santamaria International Airport (sjo) to Chicago Midway International Airport (mdw) with Southwest Airlines (WN), which offers a round-trip journey with one stop. Booking in advance is recommended, as Southwest Airlines typically offers low fares for advance bookings made within 15 days. This route is ideal for travelers looking for a budget-friendly flight option.
What's the cheapest day of the week to fly from sjo to mdw?
The cheapest day to fly from Juan Santamaria International Airport (sjo) to Chicago Midway International Airport (mdw) is Wednesday. Flying on this day can help you secure a budget-friendly flight. For a luxurious experience, consider booking a First cabin suite, which is available on this route. Booking in advance, at least 15 days prior to your trip, can also help you find the best airfares.
What's the cheapest month to fly from sjo to mdw?
The cheapest month to fly from Juan Santamaria International Airport (SJO) to Chicago Midway International Airport (MDW) is October, as it tends to have lower airfares compared to other months. You can find budget-friendly flights during this time.
Which airline/airlines fly from sjo to mdw?
Southwest Airlines operates flights from Juan Santamaria International Airport (SJO) to Chicago Midway International Airport (MDW) with one stop. For a luxurious First class experience, you can book a suite with fine dining. Booking in advance is recommended, with 15 days prior to your trip being a good time to secure a seat.
What is the cheapest airline for flights from Juan Santamaria International Airport (SJO) to Chicago Midway International Airport (MDW)?
Southwest Airlines (WN) offers the cheapest flights for this route.
How far in advance can I book flights for a round-trip trip from Milwaukee to Chicago?
It is recommended to book flights at least 15 days in advance for the best fares.
Can I find the best fares for my trip on your website?
Yes, you can find the best fares for your trip on FareLeaders.com.
What is the difference between a busco and más search on your website?
A busco search allows you to search for flights based on your preferred airline, while a más search provides more comprehensive results.
How can I plan my trip with your agency's travel services?
You can plan your trip with our travel services by contacting our agency directly.
What is the best time to book flights for a December trip?
The best time to book flights for a December trip is in September, when fares tend to be cheaper.

San Jose (SJO) to Chicago (MDW): Airport Information

Origin Airport Juan Santamaria International , San Jose, CR
Destination Airport Chicago Midway International , Chicago, US
Distance 2200 miles

More Flight Options for San Jose (SJO) and Chicago (MDW)

Why Fareleaders for SJO to MDW Plane Tickets

Lowest Prices
Lowest Prices
Uncover the best deals on San Jose to Chicago flights by comparing fares from hundreds of airlines and agencies.
New Deals
New Deals Everyday
Get the best prices on SJO to MDW flights—we update our fares daily so you never miss a saving.
Best Travel Options
No Service Fees
Compare hundreds of San Jose to Chicago flights and secure the best deals—we never add any service fees.
Get Fare Drop Alert
Be the first to know when fares drop for the San Jose (SJO) to Chicago (MDW)
Terms and Conditions*